First enantioselective synthesis of (-)-(Z)-2,3-methano-L-glutamic acid

José M. Jiménez; Rosa M. Ortuño

doi:10.1016/0957-4166(96)00423-5

First enantioselective synthesis of (-)-(Z)-2,3-methano-L-glutamic acid

José M. Jiménez, Rosa M. Ortuño

Department of Chemistry

Research output: Contribution to journal › Article › Research › peer-review

27 Citations (Scopus)

Abstract

(-)-(Z)-2,3-Methano-L-glutamic acid, a potential mGluR agonist, has been synthesized for the first time in 40% overall yield from a homochiral amino pentenoate as an easily available precursor. A conveniently protected (-)-(Z)-cyclo-aspartic acid derivative was the key intermediate, homologation of the carboxylic acid having been accomplished via the Arndt-Eistert procedure. Copyright (C) Elsevier Science Ltd.

Original language	English
Pages (from-to)	3203-3208
Journal	Tetrahedron Asymmetry
Volume	7
Issue number	11
DOIs	https://doi.org/10.1016/0957-4166(96)00423-5
Publication status	Published - 8 Nov 1996

Access to Document

10.1016/0957-4166(96)00423-5

Fingerprint Dive into the research topics of 'First enantioselective synthesis of (-)-(Z)-2,3-methano-L-glutamic acid'. Together they form a unique fingerprint.

Cite this

@article{a7cf54ad003c4486ab42a6216a4ad8aa,

title = "First enantioselective synthesis of (-)-(Z)-2,3-methano-L-glutamic acid",

abstract = "(-)-(Z)-2,3-Methano-L-glutamic acid, a potential mGluR agonist, has been synthesized for the first time in 40% overall yield from a homochiral amino pentenoate as an easily available precursor. A conveniently protected (-)-(Z)-cyclo-aspartic acid derivative was the key intermediate, homologation of the carboxylic acid having been accomplished via the Arndt-Eistert procedure. Copyright (C) Elsevier Science Ltd.",

author = "Jim{\'e}nez, {Jos{\'e} M.} and Ortu{\~n}o, {Rosa M.}",

year = "1996",

month = nov,

day = "8",

doi = "10.1016/0957-4166(96)00423-5",

language = "English",

volume = "7",

pages = "3203--3208",

number = "11",

}

TY - JOUR

T1 - First enantioselective synthesis of (-)-(Z)-2,3-methano-L-glutamic acid

AU - Jiménez, José M.

AU - Ortuño, Rosa M.

PY - 1996/11/8

Y1 - 1996/11/8

N2 - (-)-(Z)-2,3-Methano-L-glutamic acid, a potential mGluR agonist, has been synthesized for the first time in 40% overall yield from a homochiral amino pentenoate as an easily available precursor. A conveniently protected (-)-(Z)-cyclo-aspartic acid derivative was the key intermediate, homologation of the carboxylic acid having been accomplished via the Arndt-Eistert procedure. Copyright (C) Elsevier Science Ltd.

AB - (-)-(Z)-2,3-Methano-L-glutamic acid, a potential mGluR agonist, has been synthesized for the first time in 40% overall yield from a homochiral amino pentenoate as an easily available precursor. A conveniently protected (-)-(Z)-cyclo-aspartic acid derivative was the key intermediate, homologation of the carboxylic acid having been accomplished via the Arndt-Eistert procedure. Copyright (C) Elsevier Science Ltd.

U2 - 10.1016/0957-4166(96)00423-5

DO - 10.1016/0957-4166(96)00423-5

M3 - Article

VL - 7

SP - 3203

EP - 3208

IS - 11

ER -